Cinchocaine

Cinchocaine
Names
Trade namesCincain, Nupercainal, Nupercaine, Sovcaine, others
Other namesDibucaine, percaine[1]
IUPAC name
  • 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
Clinical data
Drug classLocal anesthetic (amide)[2]
Main usesHemorrhoids, pruritus ani, minor burns, insect bites[3][4]
Side effectsRash, skin irritation[4]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Topical, intravenous (for animal euthanasia)
External links
AHFS/Drugs.comMonograph
Legal
Legal status
Chemical and physical data
FormulaC20H29N3O2
Molar mass343.471 g·mol−1
3D model (JSmol)
SMILES
  • O=C(c1c2ccccc2nc(OCCCC)c1)NCCN(CC)CC
InChI
  • InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24) checkY
  • Key:PUFQVTATUTYEAL-UHFFFAOYSA-N checkY

Cinchocaine, also known as dibucaine, is a local anesthetic used together with a corticosteroid to help with the symptoms of hemorrhoids and pruritus ani.[3] It may also be used for minor burns and insect bites.[4] It is applied to the area affected.[3]

Common side effects include rash and skin irritation.[4] Other side effects may include anaphylaxis.[4] It is an amide.[2] It is one of the stronger but also more toxic local anesthetics.[2]

Cinchocaine was first made in 1929.[1] It is available over the counter and as a generic medication.[4][5] In the United States a 30 gram tube costs about 5 USD as of 2021.[5] In the United Kingdom a version which includes a steroid costs about £6.[3]

Medical use

Cinchocaine is the active ingredient in some topical hemorrhoid creams such as Proctosedyl.[6] It is also a component of the veterinary drug Somulose, used for euthanasia of horses and cattle.

Physical properties

Cinchocaine is relatively insoluble in alkaline aqueous solutions.

See also

  • Dibucaine number

References

  1. 1 2 Woolfson, David; McCafferty, Dermot (1 March 1993). Percutaneous Local Anaesthesia. CRC Press. p. 56. ISBN 978-0-13-656372-3. Archived from the original on 11 January 2022. Retrieved 24 December 2021.
  2. 1 2 3 "MeSH Browser". meshb.nlm.nih.gov. Archived from the original on 14 May 2021. Retrieved 24 December 2021.
  3. 1 2 3 4 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 101. ISBN 978-0857114105.
  4. 1 2 3 4 5 6 "Dibucaine Monograph for Professionals". Drugs.com. Archived from the original on 4 November 2021. Retrieved 24 December 2021.
  5. 1 2 "Compare Dibucaine Prices - GoodRx". GoodRx. Archived from the original on 12 November 2016. Retrieved 24 December 2021.
  6. ↑ "Proctosedyl ointment/suppositories (cinchocaine, hydrocortisone)". Netdoctor. June 2012. Archived from the original on 25 December 2019. Retrieved 25 December 2019.
  • Abdel-Ghani N, Youssef A, Awady M (2005). "Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry". Farmaco. 60 (5): 419–24. doi:10.1016/j.farmac.2005.03.001. PMID 15910814.
  • Souto-Padron T, Lima AP, de Oliveira Ribeiro R (2006). "Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi". Parasitol Res. 99 (4): 317–20. doi:10.1007/s00436-006-0192-1. PMID 16612626. S2CID 5933459.
  • Nounou M, El-Khordagui L, Khalafallah N (2005). "Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles". Acta Pol Pharm. 62 (5): 369–79. PMID 16459486.
  • Aroti, A.; Leontidis, E. (2001). "Simultaneous Determination of the Ionization Constant and the Solubility of Sparingly Soluble Drug Substances. A Physical Chemistry Experiment ". Journal of Chemical Education. 78 (6): 786–788. doi:10.1021/ed078p786.
Identifiers:
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